Identification
- Summary
Fluocinolone acetonide is a corticosteroid used to treat skin conditions, eczematous otitis externa, diabetic macular edema, and non-infectious uveitis of the posterior segment of the eye.
- Brand Names
- Capex, Derma-Smoothe/FS, Derma-smoothe FS, Dermotic, Flac, Iluvien, Neo-synalar, Otixal, Otovel, Retisert, Synalar, Tri-luma, Yutiq
- Generic Name
- Fluocinolone acetonide
- DrugBank Accession Number
- DB00591
- Background
Fluocinolone acetonide, with the formula 6-alpha, 9-alpha-difluoro-16-alpha, 17 alpha-acetonide, is a corticosteroid that presents a high lipophilicity.8 It has been used extensively in dermatological preparations and it has also been investigated thoroughly for its use in implantable corticosteroid devices.9 This type of device containing fluocinolone acetonide was developed by Taro Pharmaceuticals and approved by FDA in May 2016.11
- Type
- Small Molecule
- Groups
- Approved, Investigational, Vet approved
- Structure
Structure for Fluocinolone acetonide (DB00591)
- Weight
- Average: 452.4882
Monoisotopic: 452.201045102 - Chemical Formula
- C24H30F2O6
- Synonyms
- 6alpha-fluorotriamcinolone acetonide
- 6alpha,9alpha-difluoro-16alpha-hydroxyprednisolone 16,17-acetonide
- 6α-fluorotriamcinolone acetonide
- 6α,9α-difluoro-16α-hydroxyprednisolone 16,17-acetonide
- acétonide de fluocinolone
- acetónido de fluocinolona
- fluocinolon acetonid
- fluocinolone 16,17-acetonide
- Fluocinolone acetonide
- fluocinoloni acetonidum
- External IDs
- NSC-92339
Pharmacology
- Indication
Fluocinolone acetonide has been used extensively in different medical areas.
-In dermatology, it is extensively used for the relief of inflammatory dermatosis, dermatitis, psoriasis, hypertrophic tissues, keloid tissues and atopic dermatitis.17
-It has been used in shampoo products as a low to medium potency corticosteroid for the treatment of seborrheic dermatitis of the scalp.12
-In ear drops, it is used as a low to medium potency corticosteroid for the treatment of chronic eczematous external otitis in adults and pediatric patients 2 years and older.13
-As an intravitreal implant, it is indicated for the treatment of diabetic macular edema with patients that have been previously treated with a course of corticosteroids and no clinically significant rise in intraocular pressure.14
-Fluocinolone acetonide was announced on October 15, 2018 to be FDA approved for the treatment of chronic non-infectious uveitis affecting the posterior segment of the eye.15
-Some reports have indicated the use of fluocinolone acetonide as a vasoprotective agent and for its use in the treatment of first-degree hemorrhoids.4
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Used in combination to treat Acute otitis media Combination Product in combination with: Ciprofloxacin (DB00537) •••••••••••• •••••• ••••• •• •••••••• •••• •••••••••••• ••••• •••••••• Used in combination to treat Allergy skin Combination Product in combination with: Gentamicin (DB00798) ••• ••• ••••• Used in combination to treat Anal fissures Combination Product in combination with: Ketocaine (DB16020) •••••••••••• •••••• ••••••••••• Treatment of Atopic dermatitis •••••••••••• Used in combination to treat Chronic disease of skin Combination Product in combination with: Gentamicin (DB00798) ••• ••• ••••• - Associated Therapies
- Contraindications & Blackbox Warnings
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Fluocinolone acetonide is a synthetic anti-inflammatory corticosteroid and thus, the effect of its interaction with the body produces vasoconstriction and suppression of membrane permeability, mitotic activity, immune response and release of inflammatory mediators.18
For its ophthalmic indications, fluocinolone acetonide is administered as intravitreal micro-insert. This preparation was observed in clinical trials to reduce the recurrence of uveitis flares by 2 fold when compared with the non treated patients even after six months after initial administration. As well the intraocular pressure seemed to increase slightly with the presence of the fluocinolone implant but it is important to monitor intraocular pressure.15
- Mechanism of action
Fluocinolone acetonide is a corticosteroid and thus, it can be inferred that it acts by inhibiting the edema, fibrin deposition, capillary dilation, leukocyte migration, capillary proliferation, fibroblast proliferation, collagen deposition, and scar formation.19
Some reports have indicated that fluocinolone acetonide presents a high binding affinity for the glucocorticoid receptor. After binding the receptor, the newly formed receptor-ligand complex translocates itself into the cell nucleus, where it binds to many glucocorticoid response elements in the promoter region of the target genes.6 This effect promotes the induction of phospholipase A2 inhibitory proteins (lipocortins). Through this mechanism of action, it is thought that fluocinolone induces mainly one of the lipocortins, annexin 1, which will later mediate the synthesis of inflammatory mediators such as prostaglandins and leukotrienes by inhibiting the release of arachidonic acid which is the precursor of all these inflammatory mediators. Hence, the induction of these proteins will prevent the release of arachidonic acid by phospholipase A2.19
Target Actions Organism AGlucocorticoid receptor agonistHumans AAnnexin A1 inducerHumans AAnnexin A2 inducerHumans AAnnexin A3 inducerHumans AAnnexin A4 inducerHumans AAnnexin A5 inducerHumans UPhospholipase A2 inhibitorHumans - Absorption
When administered as an eye implant, fluocinolone acetonide presents a sustained delivery for even 12 months in which there can be observed a sustained release.16 The concentration of fluocinolone acetonide are generally higher in the vitreous and retina with a little dispersion to the aqueous humor.10
There are reports indicating that topical administration of fluocinolone acetonide produces a percutaneous absorption which is determined by the vehicle, integrity of the epidermal barrier and the use of occlusive dressing.18
Independently of the route of administration, the systemic absorption of fluocinolone acetonide is below 0.1 ng/ml which indicates that the systemic distribution is very minimal and the effect of fluocinolone is mainly local.5
- Volume of distribution
This pharmacokinetic parameter is not relevant as the systemic absorption of fluocinolone acetonide is very minimal.
- Protein binding
This pharmacokinetic parameter is not relevant as the systemic absorption of fluocinolone acetonide is very minimal.
- Metabolism
Following absorption, fluocinolone acetonide metabolism is primarily hepatic.18 It is important to mention that the systemically absorbed dose is very minimal.10
- Route of elimination
Fluocinolone acetonide is mainly excreted by the kidneys.18 It is important to mention that the systemically absorbed dose is very minimal.10
- Half-life
The reported half-life of fluocinolone acetonide ranges between 1.3-1.7 hours.7
- Clearance
This pharmacokinetic parameter is not relevant as the systemic absorption of fluocinolone acetonide is very minimal and the concentration in urine is lower than the minimum quantitation limit.10
- Adverse Effects
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Studies to determine the carcinogenic and its effect in fertility have not been performed. It is important to consider that several corticosteroids have been shown to present genotoxic potential but fluocinolone acetonide was shown to not be genotoxic in the Ames test and mouse lymphoma TK assay.19
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbacavir Fluocinolone acetonide may decrease the excretion rate of Abacavir which could result in a higher serum level. Abametapir The serum concentration of Fluocinolone acetonide can be increased when it is combined with Abametapir. Abatacept The risk or severity of adverse effects can be increased when Fluocinolone acetonide is combined with Abatacept. Abemaciclib The metabolism of Abemaciclib can be increased when combined with Fluocinolone acetonide. Acalabrutinib The metabolism of Acalabrutinib can be increased when combined with Fluocinolone acetonide. - Food Interactions
- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Active Moieties
Name Kind UNII CAS InChI Key Fluocinolone unknown CT1IX58L9S 807-38-5 UUOUOERPONYGOS-CLCRDYEYSA-N - International/Other Brands
- Biscosal (Onta Seiyaku) / Boniderma (Boniscontro) / Co-FIuosin (Sanchez-Covisa) / Coderma (Biotrading) / Cordes F (Ichthyol) / Coriphate / Cortalar (Bergamon) / Cortiderma (Gazzini) / Cortiespec (Centrum) / Cortiphate (Tokyo Tanabe) / Cortiplastol / Cortoderm (Lennon) / Derma-Smoothe/FS / Dermaisom (Isom) / Dermalar (Teva) / Dermaplus (Ripari-Gero) / Dermil (Cifa) / Dermobeta (Amelix) / Dermobiomar (Dermologia Marina) / Dermofil (N.C.S.N.) / Dermolin (Lafare) / Dermomagis (Magis) / Dermophyl (Rougier) / Dermotergol (Wolner) / Doricum (Farmila) / Esacinone (Lisapharma) / Esilon (S.I.T.) / Eskaton (Pharma Farm. Spec) / Fellin (Gruenenthal) / Flucinar (Jelfa and Polfa) / Flucort (Syntex-Tanabe) / Fluocet (Galderma Laboratories) / Fluocinil (Coli) / Fluocinone (Panther-Osfa) / Fluocit (C.T.) / Fluoderm (Unipharm) / Fluodermol (Medosan) / Fluogisol (Washington in Italy) / Fluolar (Riva) / Fluomix (Savoma) / Fluonid (Biolab and Herbert) / Fluonide Dermica (Janus) / Fluordima (Intersint) / Fluoskin (Dessy) / Fluotrex (Savage Labs) / Fluovean (Kowa) / Fluovitef (Italfarmaco) / Fluovitif / Flupollon (Mayado Seiyaku, Kaigai and Ohta) / Fluzon (Taisho) / Futocan (Shinlon) / Gelargin (Leciva) / Gelidina (I.F.L.) / Iluvien / Intradermo (Pental) / Isnaderm (Isnardi) / Isoderma (Isola-Ibi) / Jellin (Grünenthal) / Locafluo (Recordati) / Localyn (Ricordati) / Mecloderm (ICI) / Monoderm (Pharbil) / Omniderm (Face) / Oxidermiol Fuerte (Mazuelos) / Percutina (Mitim) / Prodermin (Eufarma) / Radiocin (Radiopharma) / Roliderm (Neopharmed) / Sinalar / Sterolone (Francia) / Straderm (I.T.A.) / Synalar / Synamol / Synandone (I.C.I.) / Synandrone / Synemol (Syntex) / Synotic (Zoetis) / Synsac (MP Biomedicals, LLC) / Tefunote (Taiyo) / Topifluor (Tiber) / Ultraderm (Ecobi) / Ungovac (I.C.N.)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Capex Shampoo 0.01 % Topical Galderma 2001-02-02 2014-07-15 Canada 
Capex Kit 1 mg/1mg Topical Galderma 1984-10-12 Not applicable US 
Derma Smoothe/fs Liq 0.01% Emulsion 0.01 % Topical Hill Dermaceuticals, Inc. 1991-12-31 Not applicable Canada Derma-Smoothe/FS Oil 0.11 mg/1mL Topical Physicians Total Care, Inc. 1988-02-03 2012-06-30 US Derma-Smoothe/FS Oil 0.11 mg/1mL Topical Royal Pharmaceuticals 1995-02-16 Not applicable US - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Flac Otic Oil Oil 0.11 mg/1mL Auricular (otic) Patrin Pharma 2018-04-12 Not applicable US Fluocinolone Acetonide Cream 0.25 mg/1g Topical Teligent Pharma, Inc. 2012-12-28 Not applicable US Fluocinolone Acetonide Cream 0.1 mg/1g Topical A S Medication Solutions 1982-12-16 2013-07-03 US Fluocinolone Acetonide Oil 0.11 mg/118.28mL Topical AvKARE, Inc. 2013-12-17 2020-03-31 US Fluocinolone Acetonide Oil 0.11 mg/1mL Topical Seton Pharmaceuticals 2013-08-20 Not applicable US - Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image ฟลูซิเดอร์ม ครีม Cream 0.025 %w/w บริษัท สหแพทย์เภสัช จำกัด 2017-01-23 2020-08-24 Thailand 
- Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image ACEOTO PLUS® Fluocinolone acetonide (0.25 mg) + Ciprofloxacin hydrochloride (3 mg) Solution Auricular (otic) LABORATORIOS SALVAT S.A 2013-11-25 Not applicable Colombia 
ALBAVANCE F Fluocinolone acetonide (4 %) + Hydroquinone (0.05 %) + Tretinoin (0.01 %) Cream Immortal Pharmaceutical Laboratories 2017-09-18 2027-04-19 Indonesia 
BRAVODERM-N Fluocinolone acetonide (0.25 mg/g) + Neomycin sulfate (5 mg/g) Cream Topical Bufa Aneka 2017-11-21 2027-01-28 Indonesia CETRAXAL PLUS EAR DROPS SOLUTION Fluocinolone acetonide (0.25 mg) + Ciprofloxacin hydrochloride (3 mg) Solution Auricular (otic) HYPHENS PHARMA PTE. LTD. 2014-08-29 Not applicable Singapore 
CEXIDAL Fluocinolone acetonide (0.25 MG/ML) + Ciprofloxacin (3 MG/ML) Solution / drops Auricular (otic) Infectopharm Arzneimittel Und Consilium Gmbh 2014-07-08 Not applicable Italy 
- Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Fluocinolone Acetonide 0.01/ Niacinamide 4 Fluocinolone acetonide (0.025 g/100g) + Nicotinamide (4 g/100g) Cream Topical Sincerus Florida LLC 2019-05-13 Not applicable US Fluocinolone Acetonide 0.01% / Minoxidil 5% / Tretinoin 0.025% Fluocinolone acetonide (0.01 g/100g) + Minoxidil (5 g/100g) + Tretinoin (0.025 g/100g) Solution Topical Sincerus Florida, LLC 2019-05-09 Not applicable US Fluocinolone Acetonide 0.01% / Minoxidil 7% / Progesterone 0.1% Fluocinolone acetonide (0.01 g/100g) + Minoxidil (7 g/100g) + Progesterone (0.1 g/100g) Solution Topical Sincerus Florida, LLC 2019-05-09 Not applicable US Fluocinolone Acetonide 0.01% / Niacinamide 4% Fluocinolone acetonide (0.01 g/100g) + Nicotinamide (4 g/100g) Cream Topical Sincerus Florida LLC 2019-05-13 Not applicable US Fluocinolone Acetonide 0.025% / Lidocaine HCl Monohydrate 1% Fluocinolone acetonide (0.025 g/100g) + Lidocaine hydrochloride (1 g/100g) Gel Topical Sincerus Florida, LLC 2019-05-20 Not applicable US
Categories
- ATC Codes
- S01CA10 — Fluocinolone acetonide and antiinfectives
- S01CA — Corticosteroids and antiinfectives in combination
- S01C — ANTIINFLAMMATORY AGENTS AND ANTIINFECTIVES IN COMBINATION
- S01 — OPHTHALMOLOGICALS
- S — SENSORY ORGANS
- D07BC — Corticosteroids, potent, combinations with antiseptics
- D07B — CORTICOSTEROIDS, COMBINATIONS WITH ANTISEPTICS
- D07 — CORTICOSTEROIDS, DERMATOLOGICAL PREPARATIONS
- D — DERMATOLOGICALS
- C05AA — Corticosteroids
- C05A — AGENTS FOR TREATMENT OF HEMORRHOIDS AND ANAL FISSURES FOR TOPICAL USE
- C05 — VASOPROTECTIVES
- C — CARDIOVASCULAR SYSTEM
- S01BA — Corticosteroids, plain
- S01B — ANTIINFLAMMATORY AGENTS
- S01 — OPHTHALMOLOGICALS
- S — SENSORY ORGANS
- D07AC — Corticosteroids, potent (group III)
- D07A — CORTICOSTEROIDS, PLAIN
- D07 — CORTICOSTEROIDS, DERMATOLOGICAL PREPARATIONS
- D — DERMATOLOGICALS
- S02CA — Corticosteroids and antiinfectives in combination
- S02C — CORTICOSTEROIDS AND ANTIINFECTIVES IN COMBINATION
- S02 — OTOLOGICALS
- S — SENSORY ORGANS
- Drug Categories
- Adrenal Cortex Hormones
- Agents for Treatment of Hemorrhoids and Anal Fissures for Topical Use
- Anti-Inflammatory Agents
- Corticosteroid Hormone Receptor Agonists
- Corticosteroids
- Corticosteroids, Dermatological Preparations
- Cytochrome P-450 CYP3A Inducers
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Inducers
- Cytochrome P-450 CYP3A4 Inducers (strength unknown)
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 Enzyme Inducers
- Cytochrome P-450 Substrates
- Dermatologicals
- Drugs that are Mainly Renally Excreted
- Fused-Ring Compounds
- Hormones
- Hormones, Hormone Substitutes, and Hormone Antagonists
- Immunosuppressive Agents
- Ophthalmologicals
- Otologicals
- Pregnadienes
- Pregnanes
- Steroids
- Steroids, Fluorinated
- Vasoprotectives
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as 21-hydroxysteroids. These are steroids carrying a hydroxyl group at the 21-position of the steroid backbone.
- Kingdom
- Organic compounds
- Super Class
- Lipids and lipid-like molecules
- Class
- Steroids and steroid derivatives
- Sub Class
- Hydroxysteroids
- Direct Parent
- 21-hydroxysteroids
- Alternative Parents
- Gluco/mineralocorticoids, progestogins and derivatives / 20-oxosteroids / 11-beta-hydroxysteroids / 3-oxo delta-1,4-steroids / Halogenated steroids / Delta-1,4-steroids / Ketals / 1,3-dioxolanes / Alpha-hydroxy ketones / Secondary alcohols show 9 more
- Substituents
- 11-beta-hydroxysteroid / 11-hydroxysteroid / 20-oxosteroid / 21-hydroxysteroid / 3-oxo-delta-1,4-steroid / 3-oxosteroid / 6-halo-steroid / 9-halo-steroid / Acetal / Alcohol show 27 more
- Molecular Framework
- Aliphatic heteropolycyclic compounds
- External Descriptors
- organic heteropentacyclic compound, 11beta-hydroxy steroid, glucocorticoid, cyclic ketal, 20-oxo steroid, fluorinated steroid, 3-oxo-Delta(1),Delta(4)-steroid, 21-hydroxy steroid (CHEBI:31623)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 0CD5FD6S2M
- CAS number
- 67-73-2
- InChI Key
- FEBLZLNTKCEFIT-VSXGLTOVSA-N
- InChI
- InChI=1S/C24H30F2O6/c1-20(2)31-19-9-13-14-8-16(25)15-7-12(28)5-6-21(15,3)23(14,26)17(29)10-22(13,4)24(19,32-20)18(30)11-27/h5-7,13-14,16-17,19,27,29H,8-11H2,1-4H3/t13-,14-,16-,17-,19+,21-,22-,23-,24+/m0/s1
- IUPAC Name
- (1S,2S,4R,8S,9S,11S,12R,13S,19S)-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-6,6,9,13-tetramethyl-5,7-dioxapentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosa-14,17-dien-16-one
- SMILES
- [H][C@@]12C[C@@]3([H])[C@]4([H])C[C@H](F)C5=CC(=O)C=C[C@]5(C)[C@@]4(F)[C@@H](O)C[C@]3(C)[C@@]1(OC(C)(C)O2)C(=O)CO
References
- Synthesis Reference
Mills, J.S. and Bowers, A.; U.S. Patent 3,014,938; December 26, 1961; assigned to Syntex SA, Mexico.
- General References
- Goldstein DA, Godfrey DG, Hall A, Callanan DG, Jaffe GJ, Pearson PA, Usner DW, Comstock TL: Intraocular pressure in patients with uveitis treated with fluocinolone acetonide implants. Arch Ophthalmol. 2007 Nov;125(11):1478-85. Epub 2007 Oct 8. [Article]
- Brumm MV, Nguyen QD: Fluocinolone acetonide intravitreal sustained release device--a new addition to the armamentarium of uveitic management. Int J Nanomedicine. 2007;2(1):55-64. [Article]
- Jaffe GJ, Yang CH, Guo H, Denny JP, Lima C, Ashton P: Safety and pharmacokinetics of an intraocular fluocinolone acetonide sustained delivery device. Invest Ophthalmol Vis Sci. 2000 Oct;41(11):3569-75. [Article]
- Knoch HG, Klug W, Hubner WD: [Ointment treatment of 1st degree hemorrhoids. Comparison of the effectiveness of a phytogenic preparation with two new ointments containing synthetic drugs]. Fortschr Med. 1992 Mar 20;110(8):135-8. [Article]
- Sadiq MA, Agarwal A, Soliman MK, Hanout M, Sarwar S, Do DV, Nguyen QD: Sustained-release fluocinolone acetonide intravitreal insert for macular edema: clinical pharmacology and safety evaluation. Expert Opin Drug Saf. 2015 Jul;14(7):1147-56. doi: 10.1517/14740338.2015.1041916. Epub 2015 May 20. [Article]
- Nehme A, Lobenhofer EK, Stamer WD, Edelman JL: Glucocorticoids with different chemical structures but similar glucocorticoid receptor potency regulate subsets of common and unique genes in human trabecular meshwork cells. BMC Med Genomics. 2009 Sep 10;2:58. doi: 10.1186/1755-8794-2-58. [Article]
- Broggini M, Benvenuti C, Botta V, Broccali G: Pharmacokinetics of fluocinolone acetonide in patch versus cream formulations. Int J Clin Pharmacol Res. 1991;11(1):17-21. [Article]
- Lemke T., Williams D., Roche V. and Zito W. (2008). Foye's Principles of Medicinal Chemistry (6th) (6th ed.). Lippincott Williams & Wilkins. [ISBN:978-0-7817-6879-5]
- Becker M., Davis J. (2008). Surgical Management of Inflammatory Eye Disease. Springer. [ISBN:978-3-540-33861-1]
- Narayanan R. and Kuppermann B. (2010). Retinal pharmacotherapy. Elsevier.
- FDA approvals [Link]
- Dailymed [Link]
- Dailymed [Link]
- Dailymed [Link]
- Drugs.com [Link]
- Retina today [Link]
- Topical Fluocinolone acetonide [File]
- Topical Fluocinolone acetonide UK label [File]
- Retisert (Fluocinolone acetate) FDA label [File]
- External Links
- Human Metabolome Database
- HMDB0014729
- KEGG Drug
- D01825
- PubChem Compound
- 6215
- PubChem Substance
- 46506244
- ChemSpider
- 5980
- 4461
- ChEBI
- 31623
- ChEMBL
- CHEMBL989
- ZINC
- ZINC000003977981
- Therapeutic Targets Database
- DAP000813
- PharmGKB
- PA164754912
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Fluocinolone_acetonide
- FDA label
- Download (49.7 KB)
- MSDS
- Download (75.1 KB)
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Active Not Recruiting Treatment Diabetic Macular Edema (DME) 1 4 Completed Treatment Allergic Reaction 1 4 Completed Treatment Chronic Diabetic Macular Edema 1 4 Completed Treatment Diabetic Macular Edema (DME) 2 4 Completed Treatment Melasma 2
Pharmacoeconomics
- Manufacturers
- Alpharma us pharmaceuticals division
- E fougera div altana inc
- G and w laboratories inc
- Perrigo new york inc
- Pharmaderm div altana inc
- Pharmafair inc
- Taro pharmaceuticals inc
- Taro pharmaceuticals usa inc
- Usl pharma inc
- Allergan herbert div allergan inc
- Savage laboratories inc div altana inc
- Medicis pharmaceutical corp
- Bausch and lomb inc
- Hill dermaceuticals inc
- Galderma laboratories lp
- Bausch and lomb pharmaceuticals inc
- Morton grove pharmaceuticals inc
- Packagers
- Advanced Pharmaceutical Services Inc.
- Amend
- Bausch & Lomb Inc.
- Dispensing Solutions
- E. Fougera and Co.
- G & W Labs
- Galderma Laboratories
- Hill Dermaceuticals
- Hill Laboratories Inc.
- Major Pharmaceuticals
- Medicis Pharmaceutical Co.
- Nycomed Inc.
- Patheon Inc.
- Pharmedix
- Physicians Total Care Inc.
- Preferred Pharmaceuticals Inc.
- Qualitest
- Taro Pharmaceuticals USA
- Dosage Forms
Form Route Strength Kit Topical 1 mg/1mg Shampoo Topical 0.01 % Solution Auricular (otic) 3 mg Cream Solution Auricular (otic) Cream 0.25 mg Ointment Topical Cream Cutaneous 0.010 g Emulsion Topical 0.01 % Oil Topical 0.11 mg/1mL Oil Auricular (otic) 0.11 mg/1mL Solution Auricular (otic) 0.01 % w/v Solution / drops Auricular (otic) Solution / drops Auricular (otic) 250 MICROGRAMMI/ML Gel Topical Cream Cutaneous 0.0100 g Cream Topical 0.25 mg Ointment Topical 0.25 mg Cream 0.025 %w/w Cream Topical 0.25 mg/g Cream Topical 0.1 mg/1g Oil Auricular (otic) 0.11 mg/20mL Oil Topical 0.01 mg/100mL Oil Topical 0.11 mg/118.28mL Oil Topical 0.11 mg/118.28 mL Ointment Topical Solution Topical 0.1 mg/1mL Solution / drops Auricular (otic) 0.11 mg/1mL Solution Topical Gel Topical Cream Topical .01 % Cream Topical .025 % Ointment Topical .1 mg / g Ointment Topical 0.25 mg / g Emulsion Topical Cream Cutaneous 0.25 MG/G Shampoo Topical .01 % Gel Topical 0.025 g Implant Intravitreal 0.19 mg Implant Intravitreal 0.19 mg/1 Implant Intravitreal 190 MICROGRAMMI Implant Intravitreal 190 ug Emulsion Topical 0.25 mg/g Ointment Topical 0.25 mg/g Ointment Topical 1.667 % Spray Nasal 0.01 % Lotion Topical Lotion Topical 0.01 % Lotion Topical 0025 % Solution Spray Nasal Cream 15 G Cream 20 G Cream Topical Kit Topical Insert Vaginal Cream Rectal Suppository Rectal Suppository Topical 2 G Cream Implant Intravitreal 0.59 mg/1 Implant Intravitreal 0.59 mg Cream Topical 0.025 % W/V Cream Topical 0.025 % w/w Cream Topical 0.25 mg/1g Kit Topical 0.25 mg/1g Ointment Topical 0.025 % Ointment Topical 0.25 mg/1g Solution Topical 0.01 % Cream Topical 0.025 % Ointment Topical 0.01 % Ointment Topical .025 % Cream Topical 0.010 g Kit; solution Topical 0.1 mg/1mL Cream Topical 0.01 % Cream Cutaneous Cream Topical 0.1 mg/g Kit Topical 0.1 mg/1mL Implant Intraocular 0.18 mg/1 Implant Intravitreal 0.18 mg/1 - Prices
Unit description Cost Unit Retisert implant 21900.0USD each Synalar 0.01% Solution 60ml Bottle 108.72USD bottle Synalar 0.025% Cream 60 gm Tube 103.1USD tube Synalar 0.025% Ointment 60 gm Tube 103.1USD tube Fluocinolone Acetonide 0.01% Cream 15 gm Tube 76.61USD tube Fluocinolone Acetonide 0.01% Cream 60 gm Tube 73.5USD tube Fluocinolone Acetonide 0.025% Cream 15 gm Tube 46.1USD tube Fluocinolone Acetonide 0.025% Cream 60 gm Tube 38.99USD tube Fluocinolone Acetonide 0.025% Ointment 60 gm Tube 38.99USD tube Fluocinolone acetonide powder 35.28USD g Fluocinolone Acetonide 0.025% Ointment 15 gm Tube 33.47USD tube Fluocinolone Acetonide 0.01% Solution 60ml Bottle 20.45USD bottle Dermotic oil 0.01% ear drops 1.75USD ml Derma-smoothe-fs scalp oil 0.35USD ml DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US8247395 No 2012-08-21 2022-10-22 US US8653053 No 2014-02-18 2022-10-25 US US7939516 No 2011-05-10 2025-05-04 US US7915243 No 2011-03-29 2026-03-22 US US6217895 No 2001-04-17 2019-03-22 US US6548078 No 2003-04-15 2019-03-22 US US6375972 No 2002-04-23 2020-04-26 US US8252307 No 2012-08-28 2019-06-27 US US8871241 No 2014-10-28 2027-08-12 US US8932610 No 2015-01-13 2030-03-24 US US9849085 No 2017-12-26 2020-04-26 US US8574659 No 2013-11-05 2020-04-26 US US8574613 No 2013-11-05 2020-04-26 US US9192579 No 2015-11-24 2020-04-26 US US7998108 No 2011-08-16 2028-01-12 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 266-268 Mills, J.S. and Bowers, A.; U.S. Patent 3,014,938; December 26, 1961; assigned to Syntex SA, Mexico. water solubility Insoluble 'MSDS' logP 2.48 HANSCH,C ET AL. (1995) pKa 13.9 Graham P. (2013). An Introduction to Medicinal Chemistry. Fifth ed. Oxford. - Predicted Properties
Property Value Source Water Solubility 0.0547 mg/mL ALOGPS logP 2.47 ALOGPS logP 1.6 Chemaxon logS -3.9 ALOGPS pKa (Strongest Acidic) 13.38 Chemaxon pKa (Strongest Basic) -3.3 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 6 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 93.06 Å2 Chemaxon Rotatable Bond Count 2 Chemaxon Refractivity 111.41 m3·mol-1 Chemaxon Polarizability 44.84 Å3 Chemaxon Number of Rings 5 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9865 Blood Brain Barrier + 0.9683 Caco-2 permeable + 0.5 P-glycoprotein substrate Substrate 0.7912 P-glycoprotein inhibitor I Non-inhibitor 0.5674 P-glycoprotein inhibitor II Non-inhibitor 0.8383 Renal organic cation transporter Non-inhibitor 0.8304 CYP450 2C9 substrate Non-substrate 0.8679 CYP450 2D6 substrate Non-substrate 0.8856 CYP450 3A4 substrate Substrate 0.6964 CYP450 1A2 substrate Non-inhibitor 0.9327 CYP450 2C9 inhibitor Non-inhibitor 0.9394 CYP450 2D6 inhibitor Non-inhibitor 0.9559 CYP450 2C19 inhibitor Non-inhibitor 0.9311 CYP450 3A4 inhibitor Non-inhibitor 0.8309 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8806 Ames test Non AMES toxic 0.7682 Carcinogenicity Non-carcinogens 0.9174 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 2.7033 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9838 hERG inhibition (predictor II) Non-inhibitor 0.671
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 209.138121 predictedDarkChem Lite v0.1.0 [M-H]- 205.335921 predictedDarkChem Lite v0.1.0 [M-H]- 206.57959 predictedDeepCCS 1.0 (2019) [M+H]+ 209.168421 predictedDarkChem Lite v0.1.0 [M+H]+ 201.7887498 predictedDarkChem Lite v0.1.0 [M+H]+ 208.3033 predictedDeepCCS 1.0 (2019) [M+Na]+ 207.768921 predictedDarkChem Lite v0.1.0 [M+Na]+ 212.6199073 predictedDarkChem Lite v0.1.0 [M+Na]+ 214.63228 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- General Function
- Zinc ion binding
- Specific Function
- Receptor for glucocorticoids (GC). Has a dual mode of action: as a transcription factor that binds to glucocorticoid response elements (GRE), both for nuclear and mitochondrial DNA, and as a modula...
- Gene Name
- NR3C1
- Uniprot ID
- P04150
- Uniprot Name
- Glucocorticoid receptor
- Molecular Weight
- 85658.57 Da
References
- Nehme A, Lobenhofer EK, Stamer WD, Edelman JL: Glucocorticoids with different chemical structures but similar glucocorticoid receptor potency regulate subsets of common and unique genes in human trabecular meshwork cells. BMC Med Genomics. 2009 Sep 10;2:58. doi: 10.1186/1755-8794-2-58. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inducer
- General Function
- Structural molecule activity
- Specific Function
- Plays important roles in the innate immune response as effector of glucocorticoid-mediated responses and regulator of the inflammatory process. Has anti-inflammatory activity (PubMed:8425544). Play...
- Gene Name
- ANXA1
- Uniprot ID
- P04083
- Uniprot Name
- Annexin A1
- Molecular Weight
- 38713.855 Da
References
- Retisert (Fluocinolone acetate) FDA label [File]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inducer
- General Function
- S100 protein binding
- Specific Function
- Calcium-regulated membrane-binding protein whose affinity for calcium is greatly enhanced by anionic phospholipids. It binds two calcium ions with high affinity. May be involved in heat-stress resp...
- Gene Name
- ANXA2
- Uniprot ID
- P07355
- Uniprot Name
- Annexin A2
- Molecular Weight
- 38603.63 Da
References
- Retisert (Fluocinolone acetate) FDA label [File]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inducer
- General Function
- Phospholipase a2 inhibitor activity
- Specific Function
- Inhibitor of phospholipase A2, also possesses anti-coagulant properties. Also cleaves the cyclic bond of inositol 1,2-cyclic phosphate to form inositol 1-phosphate.
- Gene Name
- ANXA3
- Uniprot ID
- P12429
- Uniprot Name
- Annexin A3
- Molecular Weight
- 36374.85 Da
References
- Retisert (Fluocinolone acetate) FDA label [File]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inducer
- General Function
- Calcium/phospholipid-binding protein which promotes membrane fusion and is involved in exocytosis.
- Specific Function
- Calcium ion binding
- Gene Name
- ANXA4
- Uniprot ID
- P09525
- Uniprot Name
- Annexin A4
- Molecular Weight
- 35882.36 Da
References
- Retisert (Fluocinolone acetate) FDA label [File]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inducer
- General Function
- Phospholipid binding
- Specific Function
- This protein is an anticoagulant protein that acts as an indirect inhibitor of the thromboplastin-specific complex, which is involved in the blood coagulation cascade.
- Gene Name
- ANXA5
- Uniprot ID
- P08758
- Uniprot Name
- Annexin A5
- Molecular Weight
- 35936.375 Da
References
- Retisert (Fluocinolone acetate) FDA label [File]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Receptor binding
- Specific Function
- PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides, this releases glycerophospholipids and arachidonic acid that serve as the precursors of signal molecules.
- Gene Name
- PLA2G1B
- Uniprot ID
- P04054
- Uniprot Name
- Phospholipase A2
- Molecular Weight
- 16359.535 Da
References
- Emerit I, Levy A, Cerutti P: Suppression of tumor promoter phorbolmyristate acetate-induced chromosome breakage by antioxidants and inhibitors of arachidonic acid metabolism. Mutat Res. 1983 Aug;110(2):327-35. doi: 10.1016/0027-5107(83)90149-5. [Article]
- Kaszkin M, Espe U, Furstenberger G, Kinzel V: Dual effect of the phorbol ester TPA on arachidonic acid release from HeLa cells. FEBS Lett. 1988 Jun 20;233(2):244-8. doi: 10.1016/0014-5793(88)80435-6. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- SubstrateInducer
- General Function
- Vitamin d3 25-hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
- Moore CD, Roberts JK, Orton CR, Murai T, Fidler TP, Reilly CA, Ward RM, Yost GS: Metabolic pathways of inhaled glucocorticoids by the CYP3A enzymes. Drug Metab Dispos. 2013 Feb;41(2):379-89. doi: 10.1124/dmd.112.046318. Epub 2012 Nov 9. [Article]
Carriers
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Binder
- General Function
- Steroid binding
- Specific Function
- Major transport protein for glucocorticoids and progestins in the blood of almost all vertebrate species.
- Gene Name
- SERPINA6
- Uniprot ID
- P08185
- Uniprot Name
- Corticosteroid-binding globulin
- Molecular Weight
- 45140.49 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:55